A DIVERSE BLEND of UW-Milwaukee students, young professionals and long-term homeowners, Milwaukee’s East Side is a longtime destination for everything dining, shopping and nightlife. Brady Street is well known as a social hub for young people from around the city, but don’t miss old-school and up-and-coming spots along North, Oakland and Downer avenues, too.
1004 E. BRADY ST.
There’s “laid back,” and then there’s “dive bar that allows dogs” laid back. Grab a Wisconsin brew and order from your favorite Brady Street restaurant at this family-owned mainstay. The building has been a tavern since 1890, and the service and friendly vibes remain unparalleled today.
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1011 E. BRADY ST.
A Milwaukee staple for more than seven decades, Glorioso’s is an authentic Italian bakery and deli. Order pasta to-go or browse the store’s aisles for Italian kitchen essentials (including wine and spirits). Across the street is Appetito, Glorioso’s kitchen, event center and cooking school.
2961 N. OAKLAND AVE.
On the East Side, Milwaukee-style pizza fans are in one of two camps: Zaffiro’s or Lisa’s. We love both, but this quintessential neighborhood joint serves quintessential Milwaukee-style pies: handcrafted thin crust with sweet sauce and fresh ingredients cut into squares the perfect size for just one more.
4. Lake Park
3233 E. KENWOOD BLVD.
Picturesque stretches of meadow, wooded paths and stunning lake views make this park an all-time favorite. Pick a sunny day to follow a ravine all the way to Bradford Beach, then reward yourself with a drink at one of the tiki huts.
We asked Dane Baldwin, owner and chef at The Diplomat (815 E. Brady St.) for his East Side highlights:
2559 N. DOWNER AVE.
If The Diplomat nourishes the body, Boswell’s nostalgic vibe, thousands of titles and author events nourish the soul. “It’s a nice, quiet bookstore, and I like to go there to peruse rather than get a specific book,” says Baldwin. “Over the years, I’ve purchased many cookbooks there.”
6. Bandit MKE
1224 E. BRADY ST.
Not far from Baldwin’s restaurant is this vintage and modern shop, which sells unique clothes, accessories and gifts focused on sustainability and inclusivity. If you want to fund your vintage habit or earn some cash, Bandit buys pre-loved clothes from the early 20th century to Y2K.
7. Strange Town
2101 N. PROSPECT AVE.
Baldwin’s a big fan of this trendy but relaxed restaurant, which serves plant-based food and natural wines in a minimalist space. It also has a great sidewalk patio for summer. “I like the vibe of the people who work there, the light that comes through the window, and the food on the plate,” he says. “It’s the perfect amount of easygoing.”